This study illustrates the regularity with which the children of mostly Mexican immigrants in Chicago interpret languages and cultural practices for their families. It also tests the hypothesis, generated from qualitative research, that such "language brokering" is related to academic outcomes. Using data collected from a subset of children (n = 87), longitudinal regression models, which controlled for early school performance, showed that higher levels of language brokering were significantly linked to better scores on fifth- and sixth-grade standardized reading tests. We suggest studying how to cultivate similar experiences at school to improve bilingual students' achievements. We also call for further mixed-method studies on this topic.